Skip to content
English

Furocoumarins in food

  • May 21, 2024

Furocoumarins are phototoxic compounds found in certain plants, food products, and cosmetics. Their potential presence in our diet raises questions about food safety and regulation.

Furocoumarins testing

Summary :

1) What are furocoumarins ?

2) Which foods may contain furocoumarins?

3)What are the standards for furocoumarins in food products ?

4) What methods are available for analyzing furocoumarins?

5) Which laboratories analyze furocoumarins in food and cosmetics?

 

 

What are furocoumarins ?

Furocoumarins, or furanocoumarins, are natural organic compounds present in certain plants (phytotoxins). They act as a defense and resistance mechanism for plants under various stress conditions such as pests, bacteria, and herbivores (phytoalexins).

Furocoumarins are phototoxic, meaning they become extremely reactive with nucleic acids and proteins in the presence of UV radiation, both after skin contact (phytophotodermatitis) and after ingestion. It is now well established that there is a link between certain skin cancers and exposure to furocoumarins when combined with UV radiation.

Furocoumarins consist of a furan ring associated with a coumarin. The position of the furan ring (6.7, 7.8, etc.) generates a wide variety of isomers, including psoralen, angelicin, and bergapten. These compounds are never found isolated and pure in nature but rather as "mixtures" of isomers, with the distribution depending on the type of plant.

These molecules fall into two major categories:

  • Angular furocoumarins have a closed cyclic structure (e.g., angelicin, found in Apiaceae).
  • Linear furocoumarins have an open structure (e.g., psoralens, primarily found in Rutaceae).


Furocoumarines

List of Major Furocoumarins

  • Angelicin (CAS No: 523-50-2)
  • Bergamottin (CAS No: 7380-40-7)
  • Bergapten (5-MOP) (CAS No: 484-20-8)
  • Bergaptol (CAS No: 486-60-2)
  • Byakangelicol (CAS No: 61046-59-1)
  • Byakangelicin (CAS No: 482-25-7)
  • Epoxybergamottin (CAS No: 206978-14-5)
  • Heraclenin (CAS No: 35740-18-2)
  • Imperatorin (CAS No: 482-44-0)
  • Isobergapten (CAS No: 482-48-4)
  • Isoimperatorin (CAS No: 482-45-1)
  • Isopeucedanin (CAS No: 482-27-9)
  • Oxypeucedanin (CAS No: 737-52-0)
  • Hydrated Oxypeucedanin (CAS No: 2643-85-8)
  • Pellopterin (CAS No: 2543-94-4)
  • Psoralen (8-MOP) (CAS No: 66-97-7)
  • 8-Geranyloxypsoralen (CAS No: 7437-55-0)
  • Xanthotoxin (CAS No: 298-81-7)
  • Xanthotoxol (CAS No: 2009-24-7)
  • 6’,7’-Dihydroxybergamottin (CAS No: 145414-76-2)

    Furocoumarins testing labs

 

Which foods may contain furocoumarins?

Furocoumarins are considered natural “toxins” and are found in a wide variety of plants consumed by humans, mainly in the Apiaceae, Moraceae, Fabaceae and Rutaceae families.

Common foods containing furocoumarins include :

  • parsley,
  • dill
  • carrots
  • celery
  • parsnips
  • figs (sap),
  • coriander,
  • cumin,
  • fennel,
  • tonka beans,
  • citrus fruits (zest, juice, drinks, tea, alcohol, marmalade, etc.)


Citrus fruits contain relatively high concentrations of furocoumarins. Each type of citrus fruit contains a different distribution of furocoumarin isomers and derivatives. Furocoumarins are mainly found in zest, and the most significant dietary exposure is from citrus juices (grapefruit, lime), citrus-based drinks and macerated citrus-based alcoholic beverages (limoncello, bergamino) and, of course, essential oils.

Some herbal food supplements (e.g. Angelica archangelica L) may contain furocoumarins, which remain “substances to be monitored” as defined in the Plant Order of June 24, 2014.

 

Use a Software Truly Designed for Quality Control!

 

What are the standards for furocoumarins in food products ?

 

There are no official standards or limits for furocoumarins in foods [1].

A persistent challenge in research on dietary exposure to furocoumarins lies in the lack of comprehensive data on furocoumarin levels in foods, which makes risk analysis difficult. Consequently, only a few studies to date have attempted to assess dietary intake of furocoumarins, and the estimates obtained vary [2].

Some daily dietary exposure data have been put forward for furocoumarins [6]:

1.30 mg/day/person (USA)
1.45 mg/day/person (Germany)
1.20 mg/day/person (UK)



In dietary supplements, furocoumarins are among the substances to be monitored in the french arrêté plantes  of June 24, 2014 , and they must be included in control plans.

 

Scientific Name Family Common Name Used Parts Substances to Monitor
Angelica archangelica L. Apiaceae Garden Angelica Leaf, fruit, rhizome, root Furocoumarins, coumarins
Angelica dahurica (Hoffm.) Benth. & Hook.f. ex Franch. & Sav. Apiaceae Bai Zhi Root Furocoumarins, coumarins
Angelica pubescens Maxim. Apiaceae Shishiudo, Du Huo Root, rhizome, leaf Furocoumarins
Angelica sinensis (Oliv.) Diels Apiaceae Chinese Angelica, Dong Quai Root Carvacrol, safrole, isosafrole, furocoumarins
Citrus aurantium L. Rutaceae Bitter Orange, Bigarade Orange, Curaçao Orange Leaf, flower, fruit, pericarp (peel or zest) Furocoumarins, p-synephrine, octopamine
Citrus limon (L.) Burm. f. Rutaceae Lemon Tree, Lemon Fruit, leaf, flower, pericarp (peel or zest) Furocoumarins
Citrus reticulata Blanco Rutaceae Mandarin Orange Fruit, pericarp (peel or zest) Furocoumarins
Citrus paradisi Macfad. Rutaceae Grapefruit Tree, Pomelo Fruit, seed (pip), pericarp (peel or zest) Furocoumarins
Ficus carica L. Moraceae Common Fig False fruit, leaf, leaf bud, stem Furocoumarins (psoralen, bergapten)
Pimpinella anisum L. Apiaceae Anise Fruit Estragole, furocoumarins
Pimpinella major (L.) Huds. Apiaceae Greater Burnet-Saxifrage Leaf, root Furocoumarins
Pimpinella saxifraga L. Apiaceae Lesser Burnet-Saxifrage Leaf, root, young shoot, seed Furocou

 

Regarding essential oils considered traditional in human food: here is the list of plants whose furocoumarins are considered as substances at risk : source DGCCRF - January 2019

Plants Common Name Risk Substances
Angelica archangelica L. Garden Angelica Furocoumarins
Apium graveolens L. Celery Furocoumarins
Petroselinum crispum (Mill.) Nyman ex A.W. Hill Parsley Furocoumarins, Elemicin, Apiole, Myristicin
Citrus aurantium L. Bitter Orange Furocoumarins, Synephrine
Citrus bergamia Risso & Poit. Bergamot Furocoumarins
Citrus limon (L.) Osbeck Lemon Tree Furocoumarins
Citrus paradisi Macfad. Grapefruit Furocoumarins
Citrus reticulata Blanco Mandarin Orange Furocoumarins
Citrus sinensis (L.) Osbeck Orange Tree Furocoumarins

 

What methods are available for analyzing furocoumarins?

Quantification and determination of furocoumarins are mainly carried out by HPLC (LC); either HPLC-UV or now very commonly LC-MS/MS. Of course, some furocoumarins also do very well with GC-MS. A recent HPTLC method has been developed for routine quality control of citrus essential oils [ 7 ].

 

Which laboratories analyze furocoumarins in food and cosmetics?

 

 

Furocoumarins testing labs

 

 

 

sources :

 

  • [ 1 ] Arigò, A., Rigano, F., Russo, M., Trovato, E., Dugo, P., & Mondello, L. (2021). Dietary Intake of Coumarins and Furocoumarins through Citrus Beverages: A Detailed Estimation by a HPLC-MS/MS Method Combined with the Linear Retention Index System. Foods, 10(7), 1533

  • [ 2 ] Melough MM, Lee SG, Cho E, Kim K, Provatas AA, Perkins C, Park MK, Qureshi A, Chun OK. Identification and Quantitation of Furocoumarins in Popularly Consumed Foods in the U.S. Using QuEChERS Extraction Coupled with UPLC-MS/MS Analysis. J Agric Food Chem. 2017 Jun 21;65(24):5049-5055. doi: 10.1021/acs.jafc.7b01279. Epub 2017 Jun 12. PMID: 28581738; PMCID: PMC8070520.

  • [ 3 ] Kerekes D, Csorba A, Gosztola B, Németh-Zámbori É, Kiss T, Csupor D. Furocoumarin Content of Fennel-Below the Safety Threshold. Molecules. 2019 Aug 5;24(15):2844. doi: 10.3390/molecules24152844. PMID: 31387269; PMCID: PMC6696257.

  • [ 4 ] Doerper, S. (2008). Modification de la Synthèse des Furocoumarines chez Ruta graveolens L. par une Approche de Génie Métabolique. Doctoral thesis, INPL, UMR 1121, INPL-INRA

  • [ 5 ] Committee E.S. Scientific Opinion on a Qualified Presumption of Safety (QPS) approach for the safety assessment of botanicals and botanical preparations. EFSA J. 2014;12:1–38. doi: 10.2903/j.efsa.2014.3593

  • [ 6 ] SKLM (2006) Toxicological Assessment of Furocoumarins in Foodstuffs, DFG, Bonn.

  • [7] Le Borgne, E., Cicchetti, E., & Bertrand, T. (2017). Méthodes HPTLC pour l’analyse qualitative et quantitative de furocoumarines sélectionnées dans les huiles essentielles. Flavour and Fragrance Journal, Special Issue: 47th International Symposium on Essential Oils (ISEO).

 

©2024 CIKLab.com All rights reserved. 

Derniers articles

Implementing new requirement 2.5.9 of FSSC 22000 V6 with CIKLab

Starting in April 2024, version 5.1 of FSSC 22000 will be officially replaced by the new version FSSC 22000 V6.Among...

by Lionel MURAT